Discover a selection of 378 vacation rentals in Shelter Island Heights, NY that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $273 per night, and houses and cabins are popular options for a stay in Shelter Island Heights. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Shelter Island Heights
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Destination guide

The lively area of Shelter Island Heights awaits your stay

Come and experience Shelter Island Heights and its opera, entertainment and theater scene. Renowned for its island views, camping and beaches, this city welcomes all visitors. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Things to do

Activities and attractions in and around Shelter Island Heights

Are you hoping to find attractions to visit in the city? Venture out of your vacation home and experience everything that makes Shelter Island Heights a fun place to get away. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Greenport Carousel (1.3 mi / 2 km)
  • Kontokosta Winery (2.2 mi / 3.6 km)
  • Sparkling Pointe (4.9 mi / 7.8 km)
  • Sannino's Bella Vita Vineyard (6 mi / 9.6 km)
  • Raphael Winery (6.4 mi / 10.3 km)
  • Lenz Winery (6.6 mi / 10.6 km)
Weather

Seasonal weather averages in Shelter Island Heights

If you're planning a vacation around the weather, July, August, June and September are the hottest months to visit, when temperatures average 67°F.

Natural features

Exploring the natural landscape of Shelter Island Heights

Travelers enjoy Shelter Island Heights for its island views and beaches. Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Shelter Island Heights is a great place to get out in nature. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Sunset Beach (0.9 mi / 1.4 km)
  • Crescent Beach (1.2 mi / 1.9 km)
  • 67 Steps Beach (2.6 mi / 4.2 km)
  • Orient Beach State Park (5.6 mi / 9.1 km)
  • Orient Point County Park (7.9 mi / 12.7 km)
  • LongHouse Reserve (10.8 mi / 17.3 km)
How to get there

Transportation to and around Shelter Island Heights

The nearest airport is in MacArthur Airport (ISP), located 43.7 mi (70.4 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into East Hampton, NY (HTO), which is 10.2 mi (16.4 km) away.

What are the top vacation rentals in or near Shelter Island Heights?

Whatever you're looking for in a getaway, you'll find a rental property in or around Shelter Island Heights that's right up your alley. Here are some of our favorites:

  • Make use of conveniences like a washing machine and lowered locks at "Beach House With Short Walk To Ditch Plains Beach". Located around 20 miles from Shelter Island Heights, this unique option has 2 bedrooms and good guest reviews.
  • Alternatively, get comfortable at "Private And Spacious Five Room Suite Steps To Bay Beach And Walk To Village". Located around 2 miles from the heart of Shelter Island Heights, it has 2 bedrooms and comes with nearby museums and outdoor furniture.

For even more great options, use the search bar at the top of the page to find the perfect Shelter Island Heights vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Shelter Island Heights?

Clock out on Friday afternoon and then forget all your worries. If you're up for some fun and relaxation, these escapes in and near Shelter Island Heights promise a memorable weekend getaway:

  • Enjoy a refreshing change of scenery at "New House, 6bd, 5bth, 4200sqft", which is around 25 miles to the southwest of Shelter Island Heights. There's lots of adventure and nature to keep you occupied here. Try kayaking and fishing or just enjoy the sights of Ocean Beach and Town of Brookhaven Wildlife and Ecology Center.
  • Alternatively, enjoy a rejuvenating getaway at "Southold Waterfront Complete With Boat Dock". Stay in and relax, or head out and try your hand at some golf and cycling. When it's time to explore some nearby attractions, check out Swan Lake Golf Club and Shell Beach. This charming vacation rental is around 4 miles southwest of Shelter Island Heights.

Can I find studio apartments for rent in and around Shelter Island Heights?

Studio apartments are a hard act to beat when it comes to location, convenience and character. Browse these studio apartments for rent in or near Shelter Island Heights and experience the local culture and vibe:

  • Explore the world around you and then sleep soundly at "Waterfront Enchanted Cottage". This vacation rental is a wonderful base for sightseeing and comes with amenities including a playground and a garden.
  • "American Beech - Deluxe King 5" is another awesome choice. Get comfortable and enjoy the use of a fridge, daily housekeeping services and more.

When you're ready to step out of your studio apartment and do some exploring, there's loads to keep you on the move around Shelter Island Heights. Interested in cultural attractions? Visit Theatre Three and Patchogue Theatre for the Performing Arts.

Can I find short term rentals in or near Shelter Island Heights?

Yes, you can. Vrbo's short-term rentals in Shelter Island Heights provide an excellent alternative to your typical cookie-cutter hotel room. Offering many of the creature comforts of home, you'll be able to shift into vacation mode the minute you arrive. Try these fabulous rentals on for size:

  • Conveniently located within easy reach of favorite attractions like Splish Splash Water Park, "Porch On Front~ Greenport Village 1st Floor Apartment" will make the ideal home away from home during your short stay in Shelter Island Heights.
  • Or maybe "Waterfront Cottage Perfection" is more your style. Visit nearby sights like Tanger Outlet Center during the daytime and then rest and relax in your comfy digs at night.

What are the best romantic weekend getaways in or near Shelter Island Heights?

Nothing says "I love you" quite like planning a romantic weekend together. If you want to spend a couple of nights away with your sweetie, we've got some romantic getaways in and around Shelter Island Heights that will sweep you off your feet:

  • Sneak away on Friday afternoon for a couple of nights of passion at "Beach House With Short Walk To Ditch Plains Beach". Around 20 miles from Shelter Island Heights, it comes with plenty of nice touches, like beauty services and winery tours.
  • Alternatively, spend your escape enjoying each other's company at "Private And Spacious Five Room Suite Steps To Bay Beach And Walk To Village", around 2 miles from Shelter Island Heights. A nearby bay and winery tours will help ramp up the romance.

Are there mansions for rent in or near Shelter Island Heights?

Nothing says "best vacation evvv-er" like staying in a mansion. Spoil the family with a memorable getaway at one of these mansions for rent in or near Shelter Island Heights:

  • Charm, elegance and oodles of character — "Ultimate Hamptons Vacation Mansion" has it all, and then some. Around 10 miles southeast of Shelter Island Heights and offering a fireplace and a swimming pool, this place is hard to beat.
  • Alternatively, score major Brownie points and settle into "Mansion Near The Bay. 7 Bedrooms Chef’s Kitchen". It's situated 7 miles to the south of Shelter Island Heights and offers amenities like a swimming pool, a firepit and more.

What are the best large group vacation rentals in or near Shelter Island Heights?

Sneak a look at these large group vacation rentals in or near Shelter Island Heights and forget about leaving anyone off your invite list:

  • A range of amenities including a swimming pool and a garden make "New House, 6bd, 5bth, 4200sqft" a favorite. This popular property has 6 bedrooms and sleeps up to 12 people. From central Shelter Island Heights, it's around 25 miles away to the southwest.
  • Invite as many as 16 of your best friends to "This Large Estate On Shelter Island W Heated Pool Is The Perfect Summer Rental" and fill the place with love and laughter. This option has 7 bedrooms and is around 1 mile to the southwest of central Shelter Island Heights. It's packed with features to keep large groups happy and comfortable, such as a swimming pool and a firepit.

What are the best houses for rent with a pool in or near Shelter Island Heights?

A pool is often a must-have when choosing where to spend your vacation, especially if you're bringing the kids along. Browse these houses with a pool in or near Shelter Island Heights and spend your days splashing about:

  • Switch to vacay mode at "Beach House With Short Walk To Ditch Plains Beach", where your biggest priority will be chilling by the pool. Amenities including a dishwasher and a living room help make this escape a favorite with guests.
  • "New House, 6bd, 5bth, 4200sqft" is the sort of place you go to get away from everything and make the most of your surroundings, starting with its inviting pool. Nearby ecotour services and a smart TV are also on hand to make your stay comfortable and convenient.

Shelter Island Heights has an oceanic climate, with average summertime temperatures ranging between 70 ºF and 75 ºF. But there's no need to wait until summertime to visit. Check out the search bar at the top of the page and adjust the filters to find the perfect Shelter Island Heights vacation rental and organize your getaway for any time of year.

What are the best large family vacation rentals in or near Shelter Island Heights?

It's always more fun to share those precious memories with the folks you love the most. Whether you're planning a family trip or spending time with friends, Vrbo has a large vacation rental that suits you. Here are two of our best in and around Shelter Island Heights:

  • Sleeping up to 12 guests in 6 bedrooms, "New House, 6bd, 5bth, 4200sqft" is the perfect place to vacation with the family. This escape is 25 miles to the southwest of Shelter Island Heights and has creature comforts such as on-site watersports and childrens activities.
  • Another great choice is "Southold Waterfront Complete With Boat Dock". This property is 4 miles southwest of Shelter Island Heights and features books, a living room and more. With 3 bedrooms accommodating up to 10 people, you won't need to leave anyone off your guest list.

When you want to explore your surroundings, there are loads of family-friendly attractions in the area to keep everyone happy and entertained. Splish Splash Water Park, Long Island Aquarium and Exhibition Center and Boomers! Medford should be at the top of your to-do list.

Can I find family cabin rentals in or near Shelter Island Heights?

Spending time with family is important, which is why we'll help you find a place where you can truly connect. Book one of these family cabin rentals in or near Shelter Island Heights and make wonderful memories with your loved ones:

  • "Lagoon Lodge North Fork Charming 3bedroom Waterfront Wifi On Beach Near Greenport" - This sought-after getaway offers a dining table and nearby whale-watching activities and is located about 3 miles to the north of the center of Shelter Island Heights.
  • "Family Cabin On The North Shore Of Long Island" - Round up the troops and spend a few nights or longer at this welcoming property, which is around 25 miles to the west of Shelter Island Heights. You'll have access to childrens activities, on-site watersports and a good deal more.

For more options, use the search bar at the top of the page and adjust the filters to find the Shelter Island Heights vacation rental that's perfect for your needs.